In the new late-night HBO series Random Acts of Flyness,Terence Nance paints the black experience with a canny, kaleidoscopic brush. He explores themes like police brutality, and blackface, and the psychological impacts of white supremacy with short, creative montages and sketches (which Nance, rather artfully, refers to as “pieces”). In the pilot episode alone, there’s a montage of grotesque police violence set to chipper music; there’s a mock cable-access show for kids featuring a grim-reaper character singing and screaming about death (“Ripa the Reaper,” played by Tony-winning actress Tonya Pinkins); there’s animation, glitter, music, and surprising cameos from instantly recognizable stars, like Jon Hamm, who plays a wholesome avatar of whiteness. It’s an extension of Nance’s subconscious: trippy, expertly fragmented, and wholly original.

“Midnight is a poetic time for it to come on,” Nance said in a recent phone interview. “Like the witching hour.”

It’s difficult to compare the show to anything else in recent TV history. If pressed—forcefully, gimme-your-lunch-money pressed—one could say it has the freewheeling pace of The Eric Andre Show, mixed with the cultural centeredness and assuredness of Atlanta. It’s a wonder that the series wound up somewhere as mainstream as HBO. The network, in Nance’s opinion, gave the green light because it believed in the overall power of his distinct artistic brand. The writer-director-performer first broke out in 2012 with the Sundance hit An Oversimplification of Her Beauty, an experimental, bighearted feature executive-produced by Dream Hampton,Wyatt Cenac, and Jay-Z. He’s since directed several short films and music videos.

HBO has proven to be a malleable partner, Nance said—he’s never faced any resistance, on a creative level, from the network. If anything, he occasionally fields questions from execs who aren’t sure about certain cultural references. But not thatoften. They largely let him do what he wants, he said, operating on the principle that they’re not exactly his target audience. He imagines there’s a lot of furtive Googling going on.

“Like, in the pilot, there’s the joke about bedussy”—an N.S.F.W. term related to, ummmmmm, genitals—“but nobody from HBO asked me, like, ‘Well, what is bedussy though?’” Nance said, laughing. “So I’m assuming they either already knew, or they looked it up.” He chuckled harder. “Or maybe they just know. People be knowin.’”

Random Acts is full of these jovial motes of humor, floating amid much heavier scenes. In one piece, there’s deftly edited B-roll footage of Deborah Johnson, the activist and girlfriend of slain revolutionary Fred Hampton, split with footage of Serena Williams. It creates a historic parallel, emphasizing the dangers both women faced at the end of their pregnancies. (Johnson was about nine months pregnant and asleep with Hampton in their home when the police broke in and gunned him down; Williams faced serious complications while giving birth, amplified by nurses who downplayed and disregarded her concerns.) The maternal mortality rates for black women are extraordinarily high in this country, a statistic further complicated by the fact that black patients often receive lesser treatment for their pain compared with white patients.

Nance felt compelled to tackle this issue, not least because it affects plenty of his family members. Patriarchy, white supremacy, anti-black violence—it all “congeals in the experience of being a black woman in America attempting to have a child,” he said.

Tackling this particular vein of white supremacy is also why Nance included a piece about a white character (Hamm) directly addressing white people and their “white thoughts” (i.e. “don’t all lives matter?”). “You can’t have white supremacy without whiteness,” he said. “But also the divestment from whiteness that would have to happen for white supremacy to end, or start to end, would have to be initiated and propagated by white people.”

“It was a gift that Jon ended up being able to do it,” Nance continued. “He put layers in the piece.” Hamm was selected because TV audiences, particularly white TV audiences, have an intimate relationship with him, thanks to his lead turn on Mad Men. Thankfully, the actor was amenable to Random Acts and the nature of the piece.